


Skinny Dipping

by DRHPaints



Category: Bill Hader - Fandom, The To Do List (2013)
Genre: Bill Hader - Freeform, Cunnilingus, Explicit Language, Explicit Sexual Content, F/M, High Sex, Marijuana, One Shot, Pool Sex, Smut, Swimming Pools, Vaginal Fingering, Vaginal Sex, smoking weed
Language: English
Status: Completed
Published: 2020-08-22
Updated: 2020-08-22
Packaged: 2021-03-06 14:53:37
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,855
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26050687
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: Natalie loses her bracelet at the Boise Pool and ends up going on a date with the manager, Willy.
Relationships: Willy McLean/Original Female Character
Kudos: 7





	Skinny Dipping

Surfacing with a gasp, Natalie pushed her wet crimson hair back from her face and rubbed the water from her eyes. 

“Oh  _ shit. _ ” Touching her wrist, Natalie glanced around the pool floor, feeling around with her feet. Finding nothing, she sighed and hoisted herself out, approaching the dingy teal employee stand. Not seeing anyone, Natalie knocked on the counter.

“Um...hello?”

A tall guy with longish, dark brown hair emerged, yawning and scratching a stubbled cheek. “Yeah?”

Dripping, Natalie cleared her throat. “Do you work here?”

“I’m the manager.” Leaning lazily on the counter, he smiled. Natalie noticed his brown shirt had at least three holes and he was wearing quite possibly the ugliest sweater she’d ever seen, but when his light pink lips spread into a wide smile, she found herself admiring how cute he was, if in a rather shabby way.

“Great, well, I lost my bracelet…” Natalie gestured over her shoulder to the pool. “It’s silver with little moonstones on it. I was wondering if you could keep an eye out for it.”

He slowly nodded, and Natalie got the sense he was staring at her chest from behind his sunglasses. “Bracelet. Silver. Moonstones. Got it.” Pursing his lips, the manager walked over to the bulletin board, tore off an ancient-looking flyer and grabbed a pen. “You should, uh...probably give me your number. You know, so I can call you if we find it.”

“Oh, um...sure.” Taking the pen from his hand, Natalie leaned over and jotted down her number, a couple of drops landing on the paper from her hair as she did so.

“I’m Willy, by the way.” Extending a large hand in her direction, Natalie smiled and shook it.

“Natalie.”

Pushing his sunglasses on top of his head, Natalie saw that Willy had exceptionally pretty dark blue eyes. “Hey Natalie.” Willy grinned, holding up her number. “I’ll be sure to let you know if we come across it.”

“Thank you.” With a little wave, Natalie jumped back in, Willy’s eyes trailing after her.

***

Laying in bed, Natalie was just getting to the last chapter of her book when the phone rang. 

“I got it!” She yelled out to her roommate before lifting the receiver to her ear. “Hello?”

“Hey, is this Natalie?” 

She switched the phone to her other ear. “Speaking. May I ask who’s calling?”

A high giggle radiated over the line. “Oh man, you actually talk like that? You’re so  _ formal. _ ”

Peeved, Natalie furrowed her brow. “Okay, really, who is this?” 

“Sorry.” The unfamiliar voice chuckled. “It’s Willy. From the pool.”

“Oh!” Natalie adjusted her arms under herself. “Did you find my bracelet?”

“Oh, um...no.” Willy was quiet for a moment. “Was it valuable? Because if someone did find it, they probably pocketed it.”

Sighing, Natalie nodded even though Willy couldn’t see her. “Yeah, kinda. You’re probably right.” They were quiet for a moment, then Natalie pulled back her head, blinking. “Wait...if you didn’t find the bracelet, why are you calling?”

“Uh...well, I, um…” She heard Willy take a deep breath. “I was wondering if you wanted to hang out. Or something. Sometime.”

Smiling, Natalie rolled onto her back. “Sure, Willy, I’d like that.”

“Yeah?” She could hear the relief in his voice. “Rad. So, um...are you free tomorrow?”

“Yeah, I could do something tomorrow night. I get off work around six.” 

“Cool, so, should I pick you up around, say, seven?” Natalie agreed and gave him her address before they made their goodbyes. Grinning to herself, Natalie returned to the book but found she was more than a little distracted.

***

Double checking her makeup, Natalie smoothed her hands over her red sundress and pulled on her strappy sandals, hearing a knock at the door. She opened it to reveal Willy, hands in the pockets of his beige shorts and sporting a faded blue, white, and red striped shirt. 

Grinning, he lifted his hand in a wave. “Hey Natalie.” 

“Hey Willy.” Closing the door behind her, she followed him outside.

“Wow, you...you look really pretty.” Eyeing her up and down, Willy rubbed the back of his neck as they walked across the lawn.

Smiling, Natalie lightly touched his elbow. “Thank you.” They reached Willy’s car. Well, calling it a car was almost too generous. With doors of three different colors, nearly more rust than paint, and a door that creaked threateningly when Willy opened it for her, it was quite possibly the shittiest vehicle Natalie had ever seen. But the interior was clean and as they pulled away The Cranberries played softly on the radio, Willy tapping along on the steering wheel.

“You wanna get a burger or something?” He turned to her as they slowed at a red light.

Natalie shrugged. “Sure, sounds good.”

Parking at Big Bun, they got their food and sat down under one of the unoccupied red and white striped umbrellas. Willy took a massive bite out of his burger, humming appreciatively.

“So how long have you worked at the pool?” Natalie asked, popping a couple of fries in her mouth.

It took Willy a couple of moments to chew and swallow. “Oh, I started when I was a teenager.” Rubbing the back of his hand over his mouth, he continued. “But I’ve only been the manager for the last four years.”

Natalie took a sip of her drink. “Do you like it there?” 

Extending a sizable hand, Willy tipped it back and forth. “I mean, for the most part. It’s easy. I pretty much get to do what I want. But of course the kids can be annoying as shit.”

Chuckling, Natalie nodded. “I bet. I can’t stand kids.”

“Really?” Willy looked at her curiously.

Shaking her head in disgust, Natalie picked up her burger. “They’re the worst.”

Willy smiled and shoved a handful of fries into his mouth. “How about you? What do you do?” He asked once he was able to speak clearly.

“Oh, just a receptionist at a dental clinic. Nothing too exciting.” Natalie gave a half smile. “But a job’s a job.”

Talking and finishing their meals, Willy suggested they go for a walk through DeMeyer Park. Puttering away, they were at a stop sign when Willy’s car stalled.

”Shit. Shit.  _ Shit! _ ” He hit the steering wheel. A car behind them honked and Willy opened the door (the window wouldn’t roll down) so he could wave them around. “ _ Fuck. _ ” Closing his eyes, Willy laid his head back on the seat. “I’m really sorry to ask, but could you help me?”

And that’s how Natalie found herself bent over the driver’s seat, steering and walking alongside while Willy pushed from behind until they got his car safely against a curb.

“Fuckin’ A.” Willy scratched the back of his head. “How am I gonna get you home?”

Natalie waved a hand. “Oh, don’t worry about it. I’m less than a mile from here. It’s not a bad walk.”

Willy ran a hand over his face. “Shit, I’m sorry. This...this probably wasn’t what you were expecting, huh?”

Chuckling, Natalie shrugged. “Well, maybe not. But it’s been nice getting to know you a bit at least.”

Glancing around, Willy furrowed his brow. “Tell you what, we’re only a few blocks from the pool. You wanna go hang out there for a while?” He raised an eyebrow at her questioningly.

“Sure, that sounds nice.” 

Walking, the sounds of Willy’s flopping sandals echoed off the quiet suburban houses and it wasn’t long before they arrived at the metal teal gate. Fishing in his pocket, Willy unlocked it and held it open for her. 

“Come on.” He gestured for Natalie to follow him into the manager’s stand. It was slightly cramped inside, and she saw a pillow and blanket underneath the desk which made her look at Willy curiously, but she didn’t question him. Willy pulled out a bright red first aid kit and set it on the counter. “Do you smoke weed?” Willy asked as he flipped open the lock.

“Yeah, sometimes.” Natalie nodded.

”Cool.” Opening the box, Willy revealed assorted bandages and a half-used bottle of antiseptic, alongside a baggie of pot and a small blue and green glass pipe. Dragging a chair to the counter, Willy offered a second one to Natalie as he packed the bowl, cobalt eyes narrowed in concentration. Brushing aside the band-aids, he located the lighter, bringing the bowl to his lips, sparking it, and inhaling deeply.

“Here you go.” Willy spoke while holding the air in his lungs. Still rolling, Natalie didn’t need to light it to take a hit and the sweet smoke burned her throat on the way down, nearly causing her to cough. Passing it back and forth, it wasn’t long before Natalie felt light-headed and giddy. She didn’t smoke often, but she could tell for Willy this was a regular occurrence as he cashed the bowl and sat back calm and satisfied.

“Hey,” Natalie gazed out over the pool, then turned to him red-eyed. “We should go swimming. That would feel  _ great _ right now.”

“You are so  _ fucking high. _ ” Willy giggled, his left eye, which was already smaller than usual, shrank even more, his top teeth extended far over the bottom ones as he rocked back and forth in mirth, slapping his knee and stomping a sandalled foot. Natalie didn’t know what was so funny, but found she couldn’t stop laughing either until finally she caught her breath.

“Come on.” She swatted Willy’s shoulder. “I wanna swim.” 

Willy scratched at his stubbled cheek. “You don’t have a swimsuit.”

“So?” Natalie raised an eyebrow. “Let’s go.” Grabbing Willy by the front of his shirt, she led him out of the stand, the blue light of the pool casting distorted shadows on the walls as they walked toward the shallow end. 

Unhooking her shoes, Natalie stepped out of them. Willy crossed his arms and looked on as if he expected her to jump in wearing her clothes, and when Natalie pulled her red dress overhead and let it flutter to the ground, he swallowed, shifting his eyes nervously. Then she reached back to unhook her bra.

“Whoa, um…” Willy held out a hand. “What’re you doing?”

Bra still hanging loosely around her front, Natalie strolled up to him and pulled the hem of his shirt through her fingertips. “What? Don’t you wanna swim with me?” She lifted it slightly and Willy looked to the pool entrance. Open to the public, anyone could walk by, but glancing back at Natalie’s enticing curves, he made up his mind, tugging his shirt overhead and casting it aside. 

Fingers trailing over his firm chest for a moment, Natalie hooked her thumbs under the waistband of her panties and pushed them to the ground, kicking them aside. Nose flaring, Willy couldn’t help but stare as he unzipped his shorts and they fell. He looked at her sheepishly before discarding his boxers, but Natalie quickly saw Willy had nothing to be embarrassed about as she approached him and caught his soft lips in a languid kiss, fingers working into his long, dark hair while his hands found her waist and drew her in.

Tilting her head, Natalie explored Willy’s mouth as a large hand reached down to cup her ass, the other massaging her breast, strong and sure as Willy’s fingertips grazed her nipples. The first sign of his erection was nudging her hip when Natalie broke away, pinched his cheek, raised her eyebrows, and jumped into the pool. 

Shaking his head and laughing, Willy followed suit, whipping the water from his long hair as he emerged. Natalie splashed him and Willy opened his mouth in shock, looking personally affronted.

“Oh now you’re gonna  _ get it. _ ” Smiling mischievously, Willy narrowed his eyes and chased her around the pool, finally catching up with Natalie and dunking her under the water, causing her to shriek in protest before he scooped her up and she wrapped her legs around his waist. Holding her aloft, they floated, Natalie’s arms around his broad shoulders as she lowered her face to his. Kissing her, Willy glided backward to the pool steps.

Coming to a stop, Natalie tightened her heels at the small of Willy’s back, his stiff cock brushing between her legs as his hand caressed her breast. Other hand creeping up her ivory thigh, Willy paused a couple of inches shy of her entrance and pulled back to look in her eyes.

Red-rimmed eyes darting over her face, Willy studied her. “This okay?” 

“Yeah.” Natalie nodded before tasting his mouth again. Parting her, Willy worked minuscule circles into her flesh until the sensation of her slickness was different from that of the water surrounding them. Sneaking an arm between them, Natalie encircled his thick cock, tugging with increased pressure until Willy was thrusting into her fist. Rocking into his hand, Natalie moaned into Willy’s mouth. The weed they smoked earlier made her hyper aware of every touch passing over her skin. 

It also served to lower Natalie’s inhibitions as she clung to Willy’s broad shoulder with her free arm, mouth warm to his ear. “ _ Fuck, Willy! You’re gonna make me cum so hard! _ ”

“...really?” Surprised, Willy sat back in the water and watched as Natalie fell apart under his fingers, legs shaking and mouth gasping. Grinning, he dove in to kiss her neck while Natalie continued to jerk his cock as she recovered. Stilling her wrist, Willy removed Natalie’s hand from his cock and hooked his hands under her thighs, floating them to the shallow’s edge. 

Holding her to the wall, Willy’s forehead met hers. “Hey, I wanna go down on you. That cool?” Rubbing his thumbs at her waist, Natalie played with his sparse dark chest hair.

“Yeah, sure, but you’re not going to go underwater, are—“ But Willy’s strong hands hoisted under her ass, lifting Natalie to the pool’s edge and guiding her knees apart. Willy brushed kisses over the inside of her thighs and along her slit, and Natalie was sure she tasted at least a little like chlorine when Willy dove forward and began lapping her with his lengthy tongue. Laying back on the floor that was textured to keep people from slipping was abrasive on Natalie’s back, but she didn’t care as Willy’s hands clamped around her hips and dragged her closer to the edge, forcing her weight down on his sturdy jaw as he inhaled her. 

Inserting two fingers, Willy pulsed roughly against the soft patch of tissue as he began sucking on Natalie’s clit. Tearing at his wet hair, Natalie’s moans turned to screams, echoing oddly off the water and reverberating off the muralled walls. 

“ _ Willy! Fuck! Don’t stop! FUCK! _ ” Legs kicking in the water like she was trying to escape a sea monster, Natalie’s body convulsed, eyes rolling and mouth working soundlessly before Willy extricated himself, wet hands patting her thighs and looking satisfied at his accomplishment.

One she caught her breath, Natalie boosted herself into the water, taking Willy by the hand and leading him back to the steps.

“Mmm, I wanna fuck you now.” She grinned as she encouraged Willy to sit and straddled him, positioning herself over his cock.

Willy squeezed her ass playfully.”Oh yeah?” He raised an eyebrow.

“Yeah.” Natalie stared into his stormy blue eyes as she sank down, taking the entirety of his cock inside of her. Letting out a deep groan, Willy’s fingertips dug into her waist. Kissing the spot where his jaw met his neck, Natalie whispered, “ _ Fuck me, Willy _ .”

Willy raised his eyebrows and smiled before his face settled into an expression of determination. The thumb of one hand fiddling her clit, Willy began pounding into Natalie. In order to combat the lower gravity, they had to work together. Natalie hooked her feet behind his back, pistoning her thighs to drive herself down on Willy’s cock while steadying herself on his strong shoulders. Willy’s free hand was at the small of her back, guiding her into his lap.

“ _ Yes, Willy! Fuck! You feel so good… _ ” Natalie bounced above him, eyes closed and mouth whimpering as they sent waves spiralling through the water. Willy felt her constrict around him, her nails digging into his back as Natalie curved forward, crying out his name. Tension delicious, Willy crossed his arms behind her, hooking his fingers over her shoulders to bring Natalie as close as possible, wet stubble flush to her neck as he hammered into her.

“ _ Oh Nat! Oh fuck...I’m gonna cum! I’m gonna cum! _ ” The vulnerability of his strangled whine as Willy shot into her made Natalie ache with tenderness and she peppered every inch of his face she could reach with kisses as they sat buoyantly in the water, gulping for air.

Parting, Willy picked a wet strand of hair from her face and moved it behind her ear. “Well, that was fun.” That slow, sexy smile that Natalie had already come to find irresistible played across his lips.

“Yeah.” Natalie traced Willy’s lower lip with her thumb. “Who would’ve thought I’d be glad I lost that bracelet?” 

**Author's Note:**

> Thank you for taking the time to read! If you enjoyed this story, please leave a comment or come say hi on tumblr at fandomtransmandom


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